I dunno. I always thought that wearing black leather meant you were trying too damn hard. It is FATAL to be perceived as trying too hard to be cool.
Leather jackets are okay if you used to fly aerial battles over Passchendaele in World War I, and you hated to throw the jacket away after the Armistice. (If that’s the case, you can also get away with wearing the fur-lined leather helmet and goggles.) Otherwise it looks like you’re trying too hard.
Go get yourself some cheap sunglasses.
'cause when you’re cool, the sun shines on you 24 hours a day. 
First of all don Jaime, you never let on how much you like a girl. “Oh, Debbie. Hi.”
Two, you always call the shots. “Kiss me. You won’t regret it.”
Now three, act like wherever you are, that’s the place to be. “Isn’t this great?”
Four, when ordering food, you find out what she wants, then order for the both of you. It’s a classy move. “Now, the lady will have the linguini and white clam sauce, and a Coke with no ice.”
And five, now this is the most important, don Jaime. When it comes down to making out, whenever possible, put on side one of Led Zeppelin IV.
My leather jacket is too small - bare wrists are only cool on girls. Silence gets me ignored. I bump into things a lot…oh. Yeah, I don’t care. Maybe that’s why I get ignored.
Might work. But isn’t Led Zep considered geeky these days?
B&W portable and a Walkman with a dead battery…check. 2000 NisMax, baby blue with the shiny wheels I had to argue with the guy to leave on the car…check. Fight Club…eh. I think Dude, Where’s My Car would get me about as far. But then, I’m still learning cool.
Check. Double check.
Fuck!
Fuck!
Okay, I’ve got some components already and know what I need to add. Anything else I need to know about? And is there anywhere to practice so I can be polished?
Trying to be cool is like chasing a butterfly, or polishing a tile for a mirror, or meditating to become a Buddha.
If you want to be cool, the first thing you must do is quit caring about whether or not you’re cool!
Think about whoever is your personal icon for cool. Do they care about being cool? If this is a celebrity chances are their image is made by committee, so it doesn’t count.
Cool is not something you have, it’s a quality observed by others while you’re doing something else. Do you like guitar? Fine! Get one a learn to play it really well. While you’re playing, you’ll be cool - until you think about how cool you are, then you’re not cool.
Buying clothes because they’re cool is not cool. Anything done in pursuit of cool drives it away. There’s a story in one of the Terry Pratchett books where the Monks of Cool have a test for cool. The candidate is shown racks and racks of the most stylish, hippest, trendiest, bleeding edge fashion and told to pick the coolest clothes in the room. The only correct answer is:
“Whatever I have on.”
Hope this helps.
[little zen bastard taking over my mind]
Not to let yourself get caught up in trying to be cool is the way. Just ask Yoda. Everybody loves Yoda. Do, or do not. There is no try. Your ‘cool’ is not my ‘cool’
My primordial nature has no liking for the life in the cities. To be free from the noise I built a little thatched cottage far away in the depth of the mountains. Wandering here and there I carry no thought. When spring comes I watch the birds; in summer I bathe in the running stream; in autumn I climb the highest peaks; during the winter I am warming up in the sun. Thus I enjoy the real flavor of the seasons.
apply this to your cool
[/little zen bastard taking over my mind]
And don’t forget your red snakeskin jacket.
punk snot dead,
broccoli!
Right, Mr. Damone. But all this didn’t help you when you were busted for scalping.
Whenever possible, emulate Zaphod Beeblebrox, the Coolest Man in the Universe.
Note: Understanding this reference is most definitely Not Cool.
I can just see Screwtape with a shaved head, kneeling next to a small gong. He strikes it and informs you to listen to the sound, find where the sound ends and the silence begins. He tells you to exist in that moment. Then proceeds to enlighten you with the contents of his post. 
He’s right too!
We have a winnah!